Cobalt-CatalyzedZtoEGeometrical Isomerization of 1,3-Dienes

被引：11

作者：

Wang, Wei ^{[1
]}

He, Shuying ^{[1
]}

Zhong, Yuqing ^{[1
]}

Chen, Jianhui ^{[1
]}

Cai, Cheng ^{[1
]}

Luo, Yanshu ^{[1
]}

Xia, Yuanzhi ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 07期

关键词：

DOUBLE-BOND ISOMERIZATION; ALKENE ISOMERIZATION; PALLADIUM(II)-CATALYZED ISOMERIZATION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC HYDROGENATION; CATALYZED ISOMERIZATION; PALLADIUM; IRON; COMPLEXES; MECHANISM;

D O I：

10.1021/acs.joc.1c03164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient cobalt-catalyzed geometrical isomerization of1,3-dienes is described. In the combination of a CoCl2precatalyst with anamido-diphosphine-oxazoline ligand, the geometrical isomerization ofE/Zmixtures of 1,3-dienes proceed in a stereoconvergent manner, affording (E)isomers in high stereoselectivity. This facile transformation features a broadsubstrate scope with good functional group tolerance and could be scaled up to the gram scale smoothly with a catalyst loading of 1mol %.

引用

页码：4712 / 4723

页数：12

共 50 条

[1] PREPARATION AND ISOMERIZATION OF 1-PHENYLSELENO 1,3-DIENES
FRYZUK, MD
BATES, GS
STONE, C
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26): : 7201 - 7211
[2] Regioselective Hydroacylation of 1,3-Dienes by Cobalt Catalysis
Chen, Qing-An
Kim, Daniel K.
Dong, Vy M.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (10) : 3772 - 3775
[3] Platinum-Catalyzed Isomerization of Cyclopropenes to 1,3-Dienes
Smyrnov, Vladyslav
Homassel, Antonin
Choudhury, Leander
Waser, Jerome
HELVETICA CHIMICA ACTA, 2024, 107 (09)
[4] RETRACTION: Chemoselective Reactions of (E)-1,3-Dienes: Cobalt-Mediated Isomerization to (Z)-1,3-Dienes and Reactions with Ethylene (Retraction of Vol 136, Pg 6215, 2014)
Timsina, Yam N.
Biswas, Souvagya
RajanBabu, T. V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (07) : 2700 - 2700
[5] HYDROSILYLATION OF 1,3-DIENES IN PRESENCE OF NICKEL AND COBALT COMPLEXES
YUREV, VP
SALIMGAREEVA, IM
ZHEBAROV, OZ
TLSTIKOV, GA
ZHURNAL OBSHCHEI KHIMII, 1976, 46 (02): : 372 - 375
[6] Cobalt-catalysed asymmetric hydrovinylation of 1,3-dienes
Timsina, Yam N.
Sharma, Rakesh K.
RajanBabu, T. V.
CHEMICAL SCIENCE, 2015, 6 (07) : 3994 - 4008
[7] Cobalt-Catalyzed Reductive Dimethylcyclopropanation of 1,3-Dienes
Werth, Jacob
Uyeda, Christopher
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (42) : 13902 - 13906
[8] HYDROSILYLATION OF 1,3-DIENES, CATALYZED BY NICKEL AND COBALT COMPLEXES
YUREV, VP
SALIMGAREEVA, IM
TOLSTIKOV, GA
ZHEBAROV, OZ
ZHURNAL OBSHCHEI KHIMII, 1975, 45 (04): : 955 - 955
[9] Isomerization of alkynes to 1,3-dienes under rhodium or palladium catalysis
Yasui, Hiroto
Yorimitsu, Hideki
Oshima, Koichiro
SYNLETT, 2006, (11) : 1783 - 1785
[10] Rhodium-catalyzed isomerization of unactivated alkynes to 1,3-dienes
Shintani, Ryo
Duan, Wei-Liang
Park, Soyoung
Hayashi, Tamio
CHEMICAL COMMUNICATIONS, 2006, (34) : 3646 - 3647

← 1 2 3 4 5 →